Daniel Kivatinos - Why This Founder Ignored Everyone and Built DrChrono Anyway

What does it actually take to build a healthcare company from scratch? In this episode of #TheShot, Eugene Borukhovich and Jim Joyce sit down with Daniel Kivatinos, co-founder of DrChrono, to unpack a real founder journey — from growing up in Queens with blue-collar parents to bootstrapping a healthcare startup through the 2008 crash, betting early on the iPad, and building DrChrono over 13+ years before selling in 2021. This is not a “how to get rich quick” story. It’s about persistence, timing, relentless shipping, and ignoring most advice. We talked about: 🧱 Start painfully small - One doctor who loves your product beats 1,000 lukewarm users 🔁 Release fast, fix faster - Daily shipping built trust doctors didn’t get from incumbents 🕰️ Timing is earned, not predicted - Years of grinding made the iPad moment possible 💸 Bootstrapping builds discipline - Scarcity forced focus 🚫 Ignore most advice - Especially from people who aren’t where you want to be 🏃‍♂️ Just do it - Overthinking kills more startups than bad ideas If you’re building in healthcare, fintech, or any regulated industry — this one’s for you. 👍 Like 📩 Subscribe 💬 Drop a comment — what resonated most? 00:00 – Intro & JP Morgan recap01:30 – Why Eugene can’t do the show without Jim02:10 – Meeting Daniel at Health 2.0 in NYC03:10 – Growing up in Queens05:00 – Blue-collar parents & elevator mechanic stories07:00 – Stony Brook, choosing computer science, brutal CS class09:30 – Art, music, and coding11:00 – Early startups that failed12:30 – The 2007–2008 reality check14:00 – Why Daniel didn’t chase “safe” jobs16:00 – Watching friends raise money & choosing a harder path18:30 – Saving $50k and deciding to start a company20:00 – Why healthcare21:00 – Founding DrChrono22:00 – What DrChrono originally solved (scheduling)23:30 – Printing flyers & knocking on doctor doors25:30 – One doctor who truly loved the product27:30 – “10 users who love you beats 1,000 who don’t”28:30 – Expanding into EHR, billing, and practice management29:30 – Hearing about the iPad30:30 – Building the first iPad-based EHR31:45 – Overnight growth after the App Store launch33:00 – Releasing faster than Epic and Cerner35:00 – Why speed mattered more than strategy36:00 – Cold-emailing Y Combinator37:00 – Alexis Ohanian visits NYC38:30 – Startup School & mindset shift39:30 – The YC interview experience40:30 – Getting the first real check41:30 – Life inside Y Combinator43:30 – Growing DrChrono over 13+ years44:30 – Selling to EverCommerce in 202145:30 – Why the buyer mattered more than the price46:30 – What Daniel is building now (JustPaid)48:00 – Why starting SMB beats selling enterprise first49:30 – Final question: advice to younger self52:00 – “Just do it. Don’t stop.”